


I'll Surely Die

by JustAn0therFang1rl



Series: It Gets Easier to Love You [5]
Category: Supernatural
Genre: F/M, Fluff, Sharing Dessert, Wow I don't know what else to tag, and a date with Dean Winchester, it's adorable, it's really just bunch of fluff, like microscopic, mild jealousy, why is that not a tag
Language: English
Status: Completed
Published: 2016-09-10
Updated: 2016-09-10
Packaged: 2018-08-14 08:10:38
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,016
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8005192
Author URL: https://archiveofourown.org/users/JustAn0therFang1rl/pseuds/JustAn0therFang1rl
Summary: <blockquote class="userstuff">
              <p>Just a really fluffy date with Dean</p>
            </blockquote>





	I'll Surely Die

**Author's Note:**

> So when I first started planning this series, I wasn't even sure if I was going to write this one because if I did, my plan was to add a little bit of Dean smut. But turns out, I was awful at writing smut. So just a really fluffy date. I guess it doesn't really have anything to do with the song, but maybe if you squint.

You stare at the slim wardrobe that you packed with you, wondering what to wear to dinner with Dean. It would help if you knew _where_ he was taking you. Do you dress up, do you dress normally, do you wear comfortable shoes or can you wear your heels? You have no clue.

Finally, you decide to go somewhere in between. You set you dark jeans and violet v-neck aside, throwing the rest back into your bag. As you start to toss your little black dress into your bag, you second guess your outfit choice. What if he takes you someplace fancy? You can’t wear jeans to a fancy restaurant. But on the other hand, you can’t wear your little black dress to a diner. You fall onto the bed, groaning.

You reach over for your phone and start scrolling through your recent calls, planning on calling Dean. That is, until you see Sam’s name.

“Hey,” Sam answers. “Everything okay?”

“Hey, Sam,” you say. “Yeah, everything’s fine. I’m just having a hard time deciding what to wear to dinner with Dean tonight.”

“So you called me?”

“Yeah. Do you have any idea where he’s taking me?” You bite your lip nervously, wondering if you should’ve just left Sam alone.

“Yeah, I do.”

You let out a silent cheer of relief.

“But Dean asked me not to tell you if you called,” Sam finishes.

“Damn, he’s smart.” You sigh. “Well, thanks anyway, Sam.”

“But, I will tell you that he’s wearing a suit. So if that helps any…”

You beam. “Thanks, Sam! So much.”

“No problem, [Y/N].”

You hang up and toss your jeans and shirt into your bag. You’re _definitely_ wearing your little black dress.

Now that you know what you’re wearing, you move onto your hair and makeup. You leave your hair natural, but pull it into a low side bun. You keep your makeup simple and easy, just putting on a little eye makeup. You almost put on lipstick, but decide against it, just sticking to your favorite lip balm.

Now, your dress. It’s this beautiful knee-length keyhole a-line dress made out of ruched chiffon with an embellished waist panel. You pair it with your favorite t-strap heels that you brought with because they’re not only cute, but comfortable.

There was a knock on your door at exactly seven. The butterflies in your stomach flutter as you go to answer.

Dean stands on the other side of the door, a bouquet of flowers in his hand, ready to greet you. But the words are caught in his throat as soon as you open the door, revealing how stunning you look.

You look at Dean with a shy smile on your face, feeling those butterflies even more with him staring at you with wide eyes.

“Hi,” you finally say.

“Wow.” Dean whistles, clearly impressed with your attire. “You look… amazing doesn’t even cover it.”

You blush. “Thank you.”

Dean holds out the flowers in front of him. “These are for you.”

You take the bouquet and inhale the fresh scent before bringing them over to the table. Without a vase, you decide to just leave the flowers as the are until you get home. You grab your clutch and double check to make sure you have your room key.

Dean escorts you to the beautiful Impala and opens the passenger’s side door for you. When he turns the engine on, classic rock starts playing on the radio. It’s loud enough to sing along, but quiet enough to still make conversation.

“You like AC/DC, right?” Dean checks.

“Who doesn’t?” you retort.

“Losers.”

The two of you chuckle together as he starts driving. You’re torn between watching Dean as he sings quietly along to the radio and watching the scenery outside.

 

Before you know it, you’re parked outside of an Italian restaurant.  You start to open your door yourself, but Dean runs around the front of the car to get it for you.

“I don’t usually come to places like this,” Dean comments once you two are seated across from one another at a table covered with white linen.

You smile. “So I should consider myself one of the lucky few to see you at a restaurant with cloth napkins?”

Dean opens his mouth to respond, but is cut off by the waitress, who seemed to have appear out of thin air from behind you.

“Hi, welcome to _Ciao Bella_! I’m Bridget, and I’ll be your server this evening.”

The way she talks directly to Dean without sparing you a single glance doesn’t go unnoticed. You suppress the urge to sigh in frustration.

“What can I get for you?” the pretty brunette asks Dean.

“Merlot for me,” Dean requests.

You wait a beat for Bridget to look over to you for your drink order, but when she doesn’t, you speak up anyway while she makes googly eyes at _your_ date.

“I’ll get the Mondavi pinot noir,” you huff, noticing the waitress walking off before you finish the word ‘pinot’. You roll your eyes.

You look up at Dean, who’s staring at you with slight concern.

“Don’t ask me what’s wrong,” you state.

“I wasn’t going to. I was waiting for you to talk about what a bitch the waitress is being.” He smiles earnestly and you can’t help but return the smile.

“I bet it’s like this pretty much everywhere you go, huh?”

Dean looks at you with mock confusion. “I don’t know what you mean. I don’t usually have a girl this beautiful with me.”

You roll your eyes again, but this time you’re still smiling.

“Any idea what you’re going to get?” Dean asks you.

You stare at your menu, skimming over all the delicious looking options.

“Not a clue. It all looks so good!” you rave. “And it’s all so expensive. Are you sure you can afford this?”

Dean’s apple green eyes look up at you. “I’m sure. Get anything you want.”

You lean forward and whisper, “but how much of it is fraud?” You smirk, proud to know how he usually pays for things, regardless of the fact that he himself hasn’t said anything.

“Actually, none of it, hopefully. I spent all afternoon hustling pool so that I could take you out somewhere nice.” He winks at you, and _goddamn that should be illegal_.

Dean chuckles and you wonder if you accidentally said that out loud.

Bridget returns with your wine, and you’re pleasantly surprised to see that she does in fact have your pinot noir as well.

“Have you decided on anything yet or still looking?” she asks, still only addressing Dean.

Dean looks at you. “[Y/N]? Still looking?” he asks politely, clearly trying to get the waitress to acknowledge you.

You look up at the waitress, surprised that she’s actually looking at you. Well, more like sizing you up, but it’s a start.

“Can I have a few more minutes, please?” you ask in a tone that as polite as you can muster up.

She rolls her eyes at you before giving Dean a flirty smile. “I’ll be back in a few minutes.” She saunters off, swaying her hips way too much for it to be natural. You roll your eyes again.

“What now?” Dean asks with an amused tone.

“She’s trying to get you to stare at her ass,” you comment nonchalantly.

“Why would I stare at her when I can stare at you?”

You feel your cheeks heat up and you take a sip of your wine to try to hide the redness you know is appearing.

 

While eating, you notice that Bridget comes to your table at least twice as often as she does other tables around you. She is trying so damn hard to get Dean to notice her with no avail. You decide to eat your entree as slowly as you can without being obnoxious about it, just to tick her off. You still have a fourth of your dinner on your plate when Bridget comes to clear Dean’s plate.

“I know what you’re doing,” Dean scolds playfully, looking at you through his thick eyelashes.

Now it was your turn to play innocent. “I have no idea what you’re talking about.”

“Yeah, I’m about as sure of that as I am that I didn’t purposely eat too fast to help you out a bit.” He wiggles his eyebrows suggestively before recomposing his face. “But really, that’s just poor customer service. I might not even tip her.”

You pretend to ponder that for a second. “You know, I’m usually dead set against tipping poorly for bad service, but in this case, I might have to make an exception.” You take another bite of food. “I mean, sometimes a server could just be having a bad day, so they’re not the nicest person in the universe, but what she’s doing is deliberate. You know she actually sized me up earlier.”

Dean sighs. “Poor girl. Too vain to realize that I’m just so damn crazy about the girl sitting across from me.”

You expect for your cheeks to heat up again, but they don’t. Dean seems to notice this, as his smile grows.

“So should I get you the check?” Bridget asks as you’re taking the last bite of your entree.

“Actually, we’d like to get some dessert,” Dean counters, looking at you. You bite back your smile.

Bridget looks like she’s trying so hard to keep from exploding. “What’ll it be for ya?” she asks through her teeth.

“Can I get the budino?” you ask, referring to the chocolate lava cake on the dessert menu.

“With two spoons,” Dean adds, throwing a wink at you.

“Coming right up.” Bridget stomps away.

You can’t help but chuckle at her temper tantrum. “You know, you could’ve gotten your own dessert.”

“You don’t want to share?” Dean teases.

“It’s not that I don’t want to share, I just thought that you could get something different and we split both of them,” you offer.

Dean beams. “That actually sounds wonderful. How does the seasonal cobbler sound to you?”

“Delightful.”

Bridget brings the lava cake with the scoop of vanilla ice cream on the side to your table, setting it in the center, handing each of you a spoon.

“Mm, that looks great, but can we also get the seasonal cobbler?” Dean orders.

“Coming right up.”

The two of you exchange a look as she walks off. You tuck a loose lock of hair behind your ear, still smiling like a schoolgirl. You scoop a bit of ice cream and a bit of cake in one spoonful and bring it to your lips. The heat of the lava cake and chill of the ice cream compliment each other in the most delectable way while the chocolate and vanilla mingle. You shudder at the heavenly taste.

“Wow, that good, huh?” Dean asks, his eyes significantly darker than they were just a moment ago.

“It’s better than sex,” you mumble around another bite.

“You only say that cause you haven’t had sex with me,” Dean teases. His eyes widen in embarrassment. “I’m sorry, I didn’t mean it like that. We don’t have to do anything tonight - or ever, if you don’t want to. I don’t want to do anything you’re not ready to.” He takes a large bite of cake to help get his foot out of his mouth. However, he regrets it when the molten center burns his tongue. “Son of a bitch,” he hisses. He grabs a bite of ice cream to tame the fire in his mouth.

You can’t help but giggle at him. The whole ordeal is just hilarious. But truth is, as much as you love the way that suit and tie look on Dean, you’d like to see what they look like on the floor.

Bridget brings the cobbler and leaves again without a word. She also leaves the check.

“Well, that’s a little presumptuous,” you comment through giggles.

“As much as I’d like to stay here with you forever, I really don’t want to be around her any longer than I have to.” Dean sets the now empty budino plate aside and replaces it with the cobbler.

Taking a bite of the cobbler, you nod, a smile on your face.

“My god,” you gasp.

Dean looks up at you instantly, concern on his face. “What? You okay?”

You nod quickly, eyes wide. “This is the _best_ cobbler I’ve ever had. Seriously, you better hurry up before I eat all of it.” With that, you scoop up another bite, a smirk on your face.

He tries to glower at you, but the smile on his face is giving him away. He scoops the bite from your fork onto his and shoves it in his mouth.

“Are you really so petty that you _had_ to steal it right off of my fork?”

“Yes. And you’re right. It _is_ really good.”

The two of you battle for each bite of the cobbler, smearing the fruity filling all over the plate, laughing and giggling the entire time.

“You wanna get out of here?” Dean asks you once the plate is only crumbs.

You nod excitedly. “Yeah, just let me use the ladies room real quick.” You excuse yourself to the restroom in the back of the restaurant.

Pushing the door open, you’re stunned at how they managed to make a _bathroom_ look so elegant. You walk over to stand in front of the sinks, looking into the mirror. You take a paper towel and dampen it a little bit before wiping under your eye, removing the mascara that smudged from laughing so hard. You apply a fresh coat, then do the same with your lip balm. Just to make sure your lips are extra soft.

Before you go back out to meet Dean, you wash your hands, taking advantage of the luxurious hand soap and lotion. You primp your hair quickly and turn away from the mirror, taking just one last look at how good you look in that dress.

You see Bridget standing at your table, talking, well more like flirting, with Dean. But you decide not to let it bother you. Easier said than done. You take a deep breath and puff your chest out just a little bit. Not enough so that it was obvious, but enough to make your boobs really pop.

As you approached, you could hear Bridget saying, “my number’s on there,” seductively as she slides the receipt over to Dean, letting her fingers linger on his hand.

Dean stands up, leaving the slip of paper on the table. “Thanks, but I don’t need the receipt.” He sees you coming up and reaches out to put his hand on the small of your back.

Bridget rolls her eyes and Dean starts leading you back out to the impala.

“You forgot to tip,” Bridget snides in your ear.

“Here’s a tip,” you snap back. “Don’t hit on somebody else’s date.”

You feel the waitress glare at you as you walk out, but you really don’t give a damn.

 

Sitting in the impala, listening to AC/DC, you notice that Dean drives past the motel you were staying at.

“Dean, you missed the turn,” you comment, a small sadness in your voice, not wanting the night to end just yet.

“I know.”

You turn to look at him, seeing that goddamn smirk on his face.

“So where are you taking me?” you purred.

“You wanna see something kinda cool?”

Your eyes widen slightly, getting excited. “I would _love_ to see something kinda cool.”

 

Dean pulls up in front of a really old looking building. The bricks are all dirty and even the entryway is buried in dirt, sticking out of a small hill. If it weren’t for the building behind it, you would’ve sworn he took you to a cave.

“What is this place?” you gasp, looking up at it.

“This is my pad.” He cuts the engine and comes around to open your door for you.

“You _live_ here?”

Dean shrugs. “In between hunts, yeah. It’s a pretty nice set up. Really big garage, nice kitchen… Oh, and the showers are pretty awesome, too.”

You bite your lip, wishing you had the nerve to make a flirty comment about needing to try it out. Instead, you stay quiet, letting Dean lead you to the door.

“Home sweet home.”

“Hey, back so soon?” Sam calls out.

“Sam, you remember [Y/N],” Dean replies, descending the metal staircase.

Sam looks up from his laptop in what you can only assume is the library, surprised.

“Uh, yeah. How you doing, [Y/N]?”

“Um...pretty good, I’d say,” you say as you exhale.

“So this right here is the war room,” Dean announces as you walk through the first room into the library. “This is the library.”

“I figured,” you comment.

Dean lets out a chuckle through his nose, reaching behind to take your hand. “Through that door is the kitchen.”

“You gonna show her the dungeon?” Sam teases.

“Like a _dungeon_ , dungeon? Not just a basement?” Your eyebrows raise in shock, but you’re also really curious.

“Everything but the dragon.” He turns back to wink at you.

“I’m assuming those are real too.”

“Eh, yeah. But you don’t find them roaming around Earth.”

You do a double take. “Then where do you find them?”

“This place called ‘purgatory’.”

“Like vasts of nothingness purgatory?”

Dean pauses for a moment. “More like the graveyard for monsters. When a monster dies, it goes to purgatory.”

You inhale deeply, just letting it all soak in. You’re not exactly new to the world of monsters, but boy do you still have a lot to learn.

Dean stops in front of a door with the number 11 on it.

“What’s this?” you ask.

Suddenly, Dean looks nervous, something you’ve yet to see on him. It was kinda cute. He scrapes his teeth across his bottom lip, and you can’t help but stare at it while you subconsciously lick yours.  
“This is my room.”

**Author's Note:**

> Ciao Bella is a real Italian restaurant in my hometown. I looked at the menu online before writing anything in, and the wines mentioned are available, as well as the desserts. It's all real. And yes, the budino is incredible. I don't know if it's better than sex (I'm still a virgin) but it is /really/ good.


End file.
